Search Cheap Flights to
Windsor

Photo by William E Berry Jr.

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Cheap Flights to Windsor

Fall in love at first flight with your vacation to Windsor by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Windsor on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Windsor, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Windsor

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Windsor with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the VSF airport.

What is the cheapest month to fly to Windsor?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Windsor are in , but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Windsor?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find  to choose from for your flight to Windsor.

What airport is best to fly into Windsor?

When you’re planning your trip to Windsor, convenience is the name of the game. Luckily, Windsor Lebanon Municipal Airport is nearby so you can deplane and get going on checking off everything on your Windsor must-do list.

How much are flights to Windsor?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Windsor on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as , you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Windsor?

The trick to saving a stack of cash on your flight to Windsor? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as  right now, why wait?

Windsor Flight Information
Destination airport
Windsor
Destination airport IATA code
VSF

Last Minute Hotel Deals in Windsor

Fat Sheep Farm & Cabins
Fat Sheep Farm & Cabins
3 out of 5
122 Best Rd, Windsor, VT
The price is $222 per night from May 1 to May 2
$222
includes taxes & fees
May 1 - May 2
Stay at this 3-star farm stay in Windsor. Enjoy free WiFi, free parking, and a garden. Popular attractions Hartland Public Library and Path of Life Garden are ...
9.6/10 Exceptional! (9 reviews)
I didn’t wanna leave
"Honestly as soon as I got there I knew I had made a good choice. Then I stepped into the cabin and knew I had made an excellent choice. It’s by far the cleanest place Ive stayed. I went looking for peace and quiet and I got just that. It’s silent, it’s beautiful, it’s private. Even though it’s deep ..."

Reviewed on Jan 18, 2025

Fat Sheep Farm & Cabins
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 out of 5
2617 Killington Rd, Killington, VT
The price is $134 per night from May 5 to May 6
$134
includes taxes & fees
May 5 - May 6
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
7.2/10 Good! (1,000 reviews)
Killington in Late April
"We had a great visit and ate in the restaurant, enjoyed the hot tub."

Reviewed on Apr 28, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
Align Inn Vermont
Align Inn Vermont
2.5 out of 5
5817 Woodstock Rd, Quechee, VT
The price is $132 per night from May 1 to May 2
$132
includes taxes & fees
May 1 - May 2
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,003 reviews)
Best in the WRJ/Quechee/Woodstock area!
"It is the most convenient and comfortable place in the greater WRJ/Quechee/Woodstock area, with pizza and a nice restaurant/pub right next door if you tire of driving. We've stayed here before and certainly will again. Oh, and the housekeepers are great."

Reviewed on Apr 27, 2025

Align Inn Vermont
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is $373 per night from May 26 to May 27
$373
includes taxes & fees
May 26 - May 27
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (513 reviews)
"Beautiful property restaurant and bar in the hotel are amazing. Only drawback was the room was hot and would not cool off was 74-75 the entire stay making the room a bit uncomfortable"

Reviewed on Apr 27, 2025

Woodstock Inn & Resort
The Mountain Inn at Killington
The Mountain Inn at Killington
2.5 out of 5
47 Old Mill Rd, Killington, VT
The price is $161 per night from May 1 to May 2
$161
includes taxes & fees
May 1 - May 2
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
9/10 Wonderful! (788 reviews)
"The property is really great for families. Super convenient to Killington resort (3-min drive), with an awesome view of the slopes. Awesome outdoor heated pool felt like a sauna, tasty restaurant and distillery. Very friendly and welcoming staff. Only issue was when I was walking out of the back ..."

Reviewed on Apr 27, 2025

The Mountain Inn at Killington
Courtyard by Marriott Hanover Lebanon
Courtyard by Marriott Hanover Lebanon
3 out of 5
10 Morgan Drive, Lebanon, NH
The price is $194 per night from May 11 to May 12
$194
includes taxes & fees
May 11 - May 12
Stay at this 3-star business-friendly hotel in Lebanon. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (899 reviews)
"Very convenient location to visit Dartmouth College, about 7min away. Quiet area, walking distance groceries."

Reviewed on Apr 15, 2025

Courtyard by Marriott Hanover Lebanon
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3 out of 5
485 Hotel Road, Brownsville, VT
The price is $165 per night from May 1 to May 2
$165
includes taxes & fees
May 1 - May 2
Stay at this 3-star resort in Brownsville. Enjoy an outdoor pool, a business center, and a fireplace in the lobby. Our guests praise the helpful staff in our ...
8.8/10 Excellent! (694 reviews)
Great value
"Beautiful property at Mt. Asutney. Tons of space. Nice restaurant. Looks as good in real lfe as it does in the pictures."

Reviewed on Apr 21, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Hotel Coolidge
Hotel Coolidge
3 out of 5
39 South Main Street, White River Junction, VT
The price is $143 per night from May 4 to May 5
$143
includes taxes & fees
May 4 - May 5
Stay at this 3-star business-friendly hotel in White River Junction. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,000 reviews)
"Beautiful old hotel."

Reviewed on Apr 27, 2025

Hotel Coolidge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.